JP4223925B2 - Electrophotographic photoreceptor, electrophotographic method using the same, electrophotographic apparatus, process cartridge for electrophotographic apparatus - Google Patents

Description

  The present invention relates to an electrophotographic photosensitive member in which a triphenylene derivative having a specific at least one tertiary amine is contained in a photosensitive layer, and an electrophotographic method, an electrophotographic apparatus and an electrophotographic method using the electrophotographic photosensitive member. The present invention relates to a process cartridge.

  In recent years, there has been a remarkable development in information processing system machines using electrophotography. In particular, laser printers and digital copying machines that convert information into digital signals and record information using light have significantly improved print quality and reliability. Furthermore, they have been applied to laser printers or digital copiers capable of full-color printing by fusing with high-speed technology. From such a background, it is particularly important to achieve both high image quality and high durability as a required photoreceptor function.

As photoconductors used in these electrophotographic laser printers, digital copiers, etc., those using organic photosensitive materials (OPC) are generally widely used for reasons such as cost, productivity and non-pollution. Applied. The layer structure of the OPC photoreceptor is roughly divided into a single layer type and a function separation type laminated structure. The first practical OPC, the PVK-TNF charge transfer complex type photoreceptor, was the former single layer type. On the other hand, in 1968, Hayashi and Regensburger independently invented a PVK / a-Se laminated photoconductor, later in 1977 by Melz et al., And in 1978 by Schlosser, an organic pigment dispersion layer and an organic low molecular weight dispersion polymer layer. A layered photoreceptor consisting of organic materials has been announced.
These are functionally separated from the concept of a charge generation layer (CGL) that absorbs light and generates charges, and a charge transport layer (CTL) that injects and transports charges generated by CGL and neutralizes surface charges. Also called a mold-laminated photoconductor. This development has dramatically improved sensitivity and durability compared to single-layer photoconductors. In addition, since materials having different functions, which are called charge generation materials (CGM) and charge transport materials (CTM), can be individually designed, the selection range of these materials has been greatly increased. For these reasons, the function-separated laminated photoconductor has the mainstream layer structure of the current OPC photoconductor. The mechanism of electrostatic latent image formation in the function-separated type photoconductor is that when the photoconductor is charged and then irradiated with light, the light passes through the charge transport layer and is absorbed by the charge generation material in the charge generation layer to generate a charge. . The charges generated thereby are injected into the charge transport layer at the interface between the charge generation layer and the charge transport layer, and further moved through the charge transport layer by an electric field, thereby neutralizing the surface charge of the photoconductor to form an electrostatic latent image. To form.

  However, organic photoconductors have large film scraping due to repeated use, and when the photosensitive layer film is scraped, the charged potential of the photoconductor decreases, the photosensitivity deteriorates, the soiling due to scratches on the surface of the photoconductor, image, etc. There is a strong tendency for density reduction or image quality degradation to be promoted. Therefore, the wear resistance of organic photoreceptors has been cited as a major problem. Further, in recent years, with the increase in the speed of an electrophotographic apparatus or the reduction in the diameter of the photoreceptor accompanying the downsizing of the apparatus, it has become a more important issue to improve the durability of the photoreceptor.

  As a method for improving the abrasion resistance of the photoconductor, a method for imparting lubricity to the photosensitive layer, curing it, or containing a filler, or a low molecular charge transport material (CTM) molecular dispersed polymer layer can be used. Methods using polymer charge transport materials are widely known. However, a new problem arises when the abrasion of the photosensitive layer is suppressed by these methods. That is, ozone, NOx, and other oxidizing substances that are repeatedly used on the surface of the photosensitive layer and adsorbed by the surrounding environment are adsorbed. Depending on the repeated use and use environment, the resistance of the outermost surface is lowered, and image flow (image blur), etc. Known to cause problems. Conventionally, the problem has been avoided to some extent by removing the blur generating material little by little together with the photosensitive layer. However, as described above, in order to meet the recent demand for higher resolution and higher durability, a new method has to be provided. One method of reducing these effects is to mount a heater on the photoreceptor, which is a major obstacle to downsizing the apparatus and reducing power consumption. Additives such as antioxidants are also effective means, but mere additives are those that do not have photoconductivity. Therefore, addition of a large amount to the photosensitive layer can reduce the sensitivity and increase the residual potential. It will imitate the problem of photographic characteristics. In addition, for example, an aromatic compound having a dialkylamino group as an acid scavenger is disclosed on a photoreceptor (see Patent Document 1). This compound is effective for image quality after repeated use. However, since the charge transport ability is low, it is difficult to meet the demand for high sensitivity and high speed, and the addition amount is limited.

  As described above, electrophotographic photoreceptors that have high wear resistance or have less shaving due to process design around the photoreceptor can avoid adverse effects on image quality such as image blurring and reduced resolution as side effects. Therefore, it has been difficult to achieve both high durability and high image quality. This is because a higher resistance is suitable for suppressing the occurrence of image blur, and a lower resistance is suitable for suppressing the increase in residual potential. It is difficult to solve.

JP 2000-231204 A

  An object of the present invention is to provide an electrophotographic photosensitive material that has high durability even for repeated use over a long period of time, suppresses image deterioration due to image density reduction or image blurring, and stably obtains high-quality images. To provide a body. In addition, by using these photoconductors, it is not necessary to replace the photoconductors, and it is possible to reduce the size of the apparatus accompanying high-speed printing or reducing the diameter of the photoconductor. An electrophotographic method, an electrophotographic apparatus, and an electrophotographic process cartridge are provided.

  As a result of investigations by the present inventors, the above-mentioned generation of blurring of oxidizing gas and the like is caused by including a triphenylene derivative having a tertiary amine represented by the following general formulas (1) to (3) in the photosensitive layer. We have found that problems such as image flow (image blur) caused by substances can be solved.

The reason why this compound is effective in maintaining the image quality by repeated use is not clear at present, but the alkylamino group structure contained in the structure is an oxidizing gas that is considered to be the cause of image blur. It is estimated that it has an effective suppression effect. It has also been found that high sensitivity and repeat stability are further increased by using in combination with other charge transport materials.
On the other hand, as such a compound having an alkylamino group, a stilbene compound is disclosed in JP-A-60-196768, Japanese Patent No. 2884353 and the like. However, since these have a dialkylamino group which is a substituent of a strong meso-merry effect (+ M effect) at the resonance site of the triarylamine structure which is a charge transport site, the overall ionization potential value becomes abnormally small. Therefore, the charge retention ability of the photosensitive layer used alone as the charge transport material is remarkably deteriorated from the beginning or by repeated use, and thus has a fatal drawback that it is very difficult to put it to practical use. Even when combined with other charge transport materials as in the present invention, since the ionization potential value of the stilbene compound is considerably smaller than those, the stilbene compound becomes a trap site for mobile charge, the sensitivity is remarkably low, and the residual The electrophotographic photosensitive member has a large potential.
Further, JP-A-9-95467 discloses a triphenylene derivative corresponding to the compound not containing the substituent Y1 in the general formula (1). However, since it does not have an alkylamino group structure that is presumed to have an effective suppression effect on oxidizing gas, there is no suppression effect on the occurrence of image blur.
Therefore, by satisfying the following configuration requirements, it is possible to achieve both high durability and high image quality, and provide an electrophotographic photosensitive member that can stably obtain high-quality images even after repeated use. The present inventors have provided an electrophotographic method, an electrophotographic apparatus, and an electrophotographic process cartridge capable of stably obtaining a high-quality image even in use.

  That is, the above-mentioned problem is characterized in that a photosensitive layer containing a triphenylene derivative having a tertiary amine represented by the following general formula (1) of the present invention is provided on a conductive support. An electrophotographic photoreceptor;

〔式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６は、置換もしくは無置換のアルキル基、もしくは下記一般式Ｙ１で表わされる置換基

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ are substituted or unsubstituted alkyl groups, or substituents represented by the following general formula Y1

（但し、一般式Ｙ１中、Ｒ^７は、置換もしくは無置換のアルキレン基であり、Ｒ^８、Ｒ^９は、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素環基を表わし、同一でも異なっていてもよい。但し、Ｒ^８、Ｒ^９のいずれか１つは置換もしくは無置換のアルキル基である。また、Ｒ^８、Ｒ^９は、互いに結合し窒素原子を含む置換もしくは無置換の複素環基を形成してもよい。）を表し、同一でも異なっていてもよい。但し、Ｒ^１〜Ｒ^６の少なくとも１つはＹ１である。Ｘは酸素原子、硫黄原子を表わす。〕」、
（２）「下記一般式（２）で表わされる第三級アミンを有するトリフェニレン誘導体を有効成分とする感光層が導電性支持体上に設けられていることを特徴とする電子写真感光体；

(In the general formula Y1, R ⁷ represents a substituted or unsubstituted alkylene group, and R ⁸ and R ⁹ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon ring group. May be the same as or different from each other, provided that one of R ⁸ and R ⁹ is a substituted or unsubstituted alkyl group, and R ⁸ and R ⁹ are bonded to each other and contain a nitrogen atom. An unsubstituted heterocyclic group may be formed), which may be the same or different. However, at least one of R ^{1 to} R ⁶ is Y1. X represents an oxygen atom or a sulfur atom. ]
(2) “An electrophotographic photosensitive member, wherein a photosensitive layer comprising a triphenylene derivative having a tertiary amine represented by the following general formula (2) as an active component is provided on a conductive support;

〔式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６は、置換もしくは無置換のアルキル基、もしくは下記一般式Ｙ１で表わされる置換基、

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ are a substituted or unsubstituted alkyl group, or a substituent represented by the following general formula Y1,

（但し、一般式Ｙ１中、Ｒ^７は、置換もしくは無置換のアルキレン基である。また、Ｒ^８、Ｒ^９は、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素環基を表わし、同一でも異なっていてもよい。但し、Ｒ^８、Ｒ^９のいずれか１つは置換もしくは無置換のアルキル基である。また、Ｒ^８、Ｒ^９は、互いに結合し窒素原子を含む置換もしくは無置換の複素環基を形成してもよい。）を表わし、同一でも異なっていてもよい。但し、Ｒ^１〜Ｒ^６の少なくとも１つはＹである。〕」、
（３）「下記一般式（３）で表わされる第三級アミンを有するトリフェニレン誘導体を有効成分とする感光層が導電性支持体上に設けられていることを特徴とする電子写真感光体；

(In the general formula Y1, R ⁷ is a substituted or unsubstituted alkylene group. Also, R ⁸ and R ⁹ are substituted or unsubstituted alkyl groups, substituted or unsubstituted aromatic hydrocarbon ring groups. Each of which may be the same or different, provided that one of R ⁸ and R ⁹ is a substituted or unsubstituted alkyl group, and R ⁸ and R ⁹ are bonded to each other and contain a nitrogen atom. A substituted or unsubstituted heterocyclic group may be formed), which may be the same or different. However, at least one of R ^{1 to} R ⁶ is Y. ]
(3) An electrophotographic photosensitive member characterized in that a photosensitive layer comprising a triphenylene derivative having a tertiary amine represented by the following general formula (3) as an active ingredient is provided on a conductive support;

〔式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６は、置換もしくは無置換のアルキル基、もしくは下記一般式Ｙ２で表わされる置換基、

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ are a substituted or unsubstituted alkyl group, or a substituent represented by the following general formula Y2,

（但し、一般式Ｙ２中、Ｒ^７、Ｒ^８は、置換もしくは無置換のアルキル基、置換もしくは無置換の芳香族炭化水素環基を表わし、同一でも異なっていてもよい。但し、Ｒ^７、Ｒ^８のいずれか１つは置換もしくは無置換のアルキル基である。また、Ｒ^７、Ｒ^８は、互いに結合し窒素原子を含む置換もしくは無置換の複素環基を形成してもよい。）を表し、同一でも異なっていてもよい。但し、Ｒ^１〜Ｒ^６の少なくとも１つはＹである。〕」、
（４）「感光層において、電荷輸送物質と、前記一般式（１）〜（３）で表わされる第三級アミンを有するトリフェニレン誘導体の中から少なくともいずれか１つが含有されていることを特徴とする前記第（１）項乃至第（３）項のいずれかに記載の電子写真感光体」、
（５）「前記電荷輸送物質が下記一般式（２０）で表わされるスチルベン化合物であることを特徴とする前記第（４）項に記載の電子写真感光体；

(In the general formula Y2, R ⁷ and R ⁸ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon ring group, and may be the same or different. However, R ⁷ , Any one of R ⁸ is a substituted or unsubstituted alkyl group, and R ⁷ and R ⁸ may be bonded to each other to form a substituted or unsubstituted heterocyclic group containing a nitrogen atom.) Which may be the same or different. However, at least one of R ^{1 to} R ⁶ is Y. ]
(4) “The photosensitive layer contains at least one of a charge transport material and a triphenylene derivative having a tertiary amine represented by the general formulas (1) to (3)”. The electrophotographic photosensitive member according to any one of (1) to (3),
(5) The electrophotographic photosensitive member according to item (4), wherein the charge transporting substance is a stilbene compound represented by the following general formula (20):

〔式中、ｎは０または１の整数、Ｒ^１は水素原子、アルキル基または置換もしくは無置換のフェニル基を表わし、Ａｒ^１は置換もしくは無置換の芳香族炭化水素環基を表わし、Ｒ^５は炭素数１〜４アルキル基、あるいは置換もしくは無置換の芳香族炭化水素環基を表わし、Ａｒ^１とＲ^５は共同で環を形成しても良い。Ａは式

[Wherein n represents an integer of 0 or 1, R ¹ represents a hydrogen atom, an alkyl group, or a substituted or unsubstituted phenyl group, Ar ¹ represents a substituted or unsubstituted aromatic hydrocarbon ring group, R ⁵ Represents an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring group, and Ar ¹ and R ⁵ may jointly form a ring. A is an expression

あるいは

Or

で表される置換基、
｛但し、上記式中Ｒ^２は水素原子、アルキル基、アルコキシ基、ハロゲン原子または式

A substituent represented by
{Wherein R ² is a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or a formula

（ただし、Ｒ^３およびＲ^４は置換もしくは無置換の芳香族炭化水素環基を示し、Ｒ^３およびＲ^４は同じでも異なっていてもよく、環を形成しても良い）を表わし、ｍは１〜３の整数を表わし、２以上のときＲ^２は同一でも異なっても良い。｝
９−アントリル基または置換もしくは無置換のカルバゾリル基を表わす。また、ｎが０のとき、ＡとＲ^１は共同で環を形成しても良い。〕」、
（６）「前記電荷輸送物質が下記一般式（２５）で表わされるアミノビフェニル化合物であることを特徴とする前記第（４）項に記載の電子写真感光体；

Wherein R ³ and R ⁴ represent a substituted or unsubstituted aromatic hydrocarbon ring group, and R ³ and R ⁴ may be the same or different and may form a ring, and m represents Represents an integer of 1 to 3, and R ² may be the same or different when it is 2 or more. }
It represents a 9-anthryl group or a substituted or unsubstituted carbazolyl group. When n is 0, A and R ¹ may form a ring together. ]
(6) “The electrophotographic photosensitive member according to item (4), wherein the charge transporting substance is an aminobiphenyl compound represented by the following general formula (25);

（式中、Ｒ^１、Ｒ^３およびＲ^４は水素原子、アミノ基、アルコキシ基、チオアルコキシ基、アリールオキシ基、メチレンジオキシ基、置換もしくは無置換のアルキル基、ハロゲン原子または置換もしくは無置換のアリール基を、Ｒ^２は水素原子、アルコキシ基、置換もしくは無置換のアルキル基またはハロゲン原子を表わす。また、ｋ，ｌ，ｍおよびｎは１、２、３または４の整数であり、それぞれが２、３または４の整数のときは、前記Ｒ^１、Ｒ^２、Ｒ^３およびＲ^４は同じでも異なっていても良い。）」、
（７）「前記電荷輸送物質が、高分子型電荷輸送物質であることを特徴とする前記第（４）項に記載の電子写真感光体」、
（８）「前記高分子型電荷輸送物質が下記一般式（II）で表わされる物質であることを特徴とする前記第（７）項に記載の電子写真感光体；

(Wherein R ¹ , R ³ and R ⁴ are a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted group. R ² represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, and k, l, m and n are integers of 1, 2, 3 or 4, When R is an integer of 2, 3 or 4, the R ¹ , R ² , R ³ and R ⁴ may be the same or different.
(7) “The electrophotographic photosensitive member according to (4) above, wherein the charge transporting material is a polymer type charge transporting material”,
(8) “The electrophotographic photosensitive member according to item (7), wherein the polymer charge transporting material is a material represented by the following general formula (II):

〔式中、Ｒ_７，Ｒ_８は置換もしくは無置換の芳香環基、Ａｒ_１，Ａｒ_２，Ａｒ_３は同一あるいは異なる芳香環基を表わす。ｋ，ｊは組成を表わし、０．１≦ｋ≦１、０≦ｊ≦０．９、ｎは繰り返し単位数を表わし５〜５０００の整数である。
Ｘは脂肪族の２価基、環状脂肪族の２価基、または下記一般式Ｓ１もしくはＳ２で表わされる２価基を表わす。

[Wherein R ₇ and R ₈ represent substituted or unsubstituted aromatic ring groups, and Ar ₁ , Ar ₂ and Ar ₃ represent the same or different aromatic ring groups. k, j represents the composition, 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, and n represents the number of repeating units and is an integer of 5 to 5000.
X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula S1 or S2.

（但し、一般式Ｓ１中、Ｒ_１０１，Ｒ_１０２は各々独立して置換もしくは無置換のアルキル基、芳香環基またはハロゲン原子を表わす。ｌ、ｍは０〜４の整数、Ｙは単結合、炭素原子数１〜１２の直鎖状、分岐状もしくは環状のアルキレン基、−Ｏ−，−Ｓ−，−ＳＯ−，−ＳＯ_２−，−ＣＯ−，−ＣＯ−Ｏ−Ｚ−Ｏ−ＣＯ−（式中Ｚは脂肪族の２価基を表わす。）を表わし、一般式Ｓ２中、ａは１〜２０の整数、ｂは１〜２０００の整数、Ｒ_１０３、Ｒ_１０４は置換または無置換のアルキル基又はアリール基を表わす。）ここで、Ｒ_１０１とＲ_１０２，Ｒ_１０３とＲ_１０４は、それぞれ同一でも異なってもよい。）を表わす。〕」、
（９）「前記高分子型電荷輸送物質が下記一般式（ＸＩ）で表わされる物質であることを特徴とする前記第（７）項に記載の電子写真感光体；

(In the general formula S1, R ₁₀₁ and R ₁₀₂ each independently represents a substituted or unsubstituted alkyl group, an aromatic ring group or a halogen atom. L, m are integers of 0 to 4, Y is a single bond, A linear, branched or cyclic alkylene group having 1 to 12 carbon atoms, —O—, —S—, —SO—, —SO ₂ —, —CO—, —CO—O—Z—O—CO -(Wherein Z represents an aliphatic divalent group), in general formula S2, a is an integer of 1 to 20, b is an integer of 1 to 2000, and R ₁₀₃ and R ₁₀₄ are substituted or unsubstituted. R ₁₀₁ and R ₁₀₂ , R ₁₀₃ and R ₁₀₄ may be the same or different from each other. ). ]
(9) “The electrophotographic photosensitive member according to item (7), wherein the polymer charge transporting material is a material represented by the following general formula (XI):

（式中、Ａｒ_１、Ａｒ_２、Ａｒ_３、Ａｒ_４およびＡｒ_５は置換もしくは無置換の芳香環基、Ｚは芳香環基または―Ａｒ_６―Ｚａ―Ａｒ_６―を表わし、Ａｒ_６は置換もしくは無置換の芳香環基、ＺａはＯ、Ｓまたはアルキレン基、ＲおよびＲ’は直鎖又は分岐鎖のアルキレン基を表わす。ｍは０または１を表わす。ｋ、ｊ、ｎ及びＸは前式と同じ。）」によって解決される。
また、上記課題は、本発明の（１０）「電子写真感光体に、少なくとも帯電、画像露光、現像、転写が繰り返し行われる電子写真方法において、該電子写真感光体が前記第（１）項乃至第（９）項のいずれかに記載の電子写真感光体であることを特徴とする電子写真方法」、
（１１）「電子写真感光体に、少なくとも帯電、画像露光、現像、転写を繰り返し行ない、かつ画像露光の際にはＬＤあるいはＬＥＤ等によって感光体上に静電潜像の書き込みが行われる、所謂デジタル方式の電子写真方法において、該電子写真感光体が前記第（１）項乃至第（９）項のいずれかに記載の電子写真感光体であることを特徴とする電子写真方法」によって解決される。
また、上記課題は、本発明の（１２）「少なくとも帯電手段、画像露光手段、現像手段、転写手段および電子写真感光体を具備してなる電子写真装置であって、該電子写真感光体が前記第（１）項乃至第（９）項のいずれかに記載の電子写真感光体であることを特徴とする電子写真装置」、
（１３）「少なくとも帯電手段、画像露光手段、現像手段、転写手段および電子写真感光体を具備してなる電子写真装置において、画像露光手段にＬＤあるいはＬＥＤ等を使用することによって感光体上に静電潜像の書き込みが行われる、所謂デジタル方式の電子写真装置であって、該電子写真感光体が前記第（１）項乃至第（９）項のいずれかに記載の電子写真感光体であることを特徴とする電子写真装置」によって解決される。
また、上記課題は、本発明の（１４）「少なくとも電子写真感光体を具備してなる電子写真装置用プロセスカートリッジであって、該電子写真感光体が前記第（１）項乃至第（９）項のいずれかに記載の電子写真感光体であることを特徴とする電子写真装置用プロセスカートリッジ」によって解決される。

(In the formula, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ and Ar ₅ represent a substituted or unsubstituted aromatic ring group, Z represents an aromatic ring group or —Ar ₆ —Za—Ar ₆ —, and Ar ₆ represents a substituted group. Or an unsubstituted aromatic ring group, Za represents O, S or an alkylene group, R and R ′ represent a linear or branched alkylene group, m represents 0 or 1, k, j, n and X represent Same as formula.) ”.
Further, the above-mentioned problem is (10) in the electrophotographic method in which at least charging, image exposure, development, and transfer are repeatedly performed on the electrophotographic photosensitive member. An electrophotographic method characterized in that it is an electrophotographic photosensitive member according to any one of (9),
(11) “At least charging, image exposure, development, and transfer are repeatedly performed on the electrophotographic photosensitive member, and at the time of image exposure, an electrostatic latent image is written on the photosensitive member by an LD or an LED. In a digital type electrophotographic method, the electrophotographic photosensitive member is an electrophotographic photosensitive member according to any one of the items (1) to (9). The
The above-mentioned problem is (12) “electrophotographic apparatus comprising at least a charging means, an image exposing means, a developing means, a transferring means, and an electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is the above-mentioned subject. An electrophotographic apparatus comprising the electrophotographic photosensitive member according to any one of Items (1) to (9);
(13) In an electrophotographic apparatus comprising at least a charging unit, an image exposing unit, a developing unit, a transferring unit, and an electrophotographic photosensitive member, an LD or LED is used as the image exposing unit to A so-called digital electrophotographic apparatus in which an electrostatic latent image is written, wherein the electrophotographic photosensitive member is the electrophotographic photosensitive member according to any one of (1) to (9). This is solved by an electrophotographic apparatus characterized by the above.
Further, the above-mentioned problem is (14) of the present invention, “a process cartridge for an electrophotographic apparatus comprising at least an electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is the item (1) to (9). The electrophotographic photosensitive member according to any one of the items is solved by a “process cartridge for an electrophotographic apparatus”.

  According to the present invention, by containing a triphenylene derivative having a tertiary amine represented by the general formulas (1) to (3), it can be used repeatedly and environmentally resistant to oxidizing gas without causing a decrease in sensitivity. Therefore, it is possible to obtain a photoconductor having high durability and high resolution image quality over a long period of time. According to the present invention, both high durability and high image quality of an electrophotographic photoreceptor are realized, and an electrophotographic photoreceptor capable of stably obtaining a high-quality image over a long period of time, and an electrophotographic method and electrophotography using the same An apparatus and a process cartridge for an electrophotographic apparatus are provided.

Hereinafter, the electrophotographic photosensitive member of the present invention, the electrophotographic method using the same, the electrophotographic apparatus, and the electrophotographic process cartridge will be described in detail.
First, the details of the general formulas (1) to (3) to be contained in the photosensitive layer in the present invention will be described.

  In the definition of the substituents of the general formulas (1) to (3), specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, and an undecanyl group. In addition, examples of aromatic ring groups include monovalent to hexavalent aromatic hydrocarbon groups of aromatic hydrocarbon rings such as benzene, naphthalene, anthracene, and pyrene, and pyridine, quinoline, thiophene, furan, oxazole, oxadiazole, and carbazole. And monovalent to hexavalent aromatic heterocyclic groups of an aromatic heterocyclic ring. These substituents include those exemplified in the above specific examples of alkyl groups, alkoxy groups such as methoxy group, ethoxy group, propoxy group and butoxy group, or halogen atoms of fluorine atom, chlorine atom, bromine atom and iodine atom. An atom, an aromatic ring group, etc. are mentioned. Furthermore, specific examples of the heterocyclic group bonded to each other and containing a nitrogen atom include a pyrrolidinyl group, a piperidinyl group, and a pyrrolinyl group. In addition, examples of the heterocyclic group jointly containing a nitrogen atom include aromatic heterocyclic groups such as N-methylcarbazole, N-ethylcarbazole, N-phenylcarbazole, indole, and quinoline.

  Preferred examples of general formulas (1) to (3) are given below. However, the present invention is not limited to these compounds.

Next, the layer structure of the electrophotographic photosensitive member will be described with reference to FIGS.
FIG. 1 is a cross-sectional view showing an example of an electrophotographic photosensitive member of the present invention. A photosensitive layer (33) mainly composed of a charge generating material and a charge transporting material is provided on a conductive support (31). ing.
The photoconductor of FIG. 2 has a charge generation layer (35) mainly composed of a charge generation material and a charge transport layer (37) mainly composed of a charge transport material on a conductive support (31). It has a stacked configuration.
In the photoreceptor of FIG. 3, a photosensitive layer (33) mainly composed of a charge generating substance and a charge transporting substance is provided on a conductive support (31), and a protective layer (39) is provided on the surface of the photosensitive layer. It will be.
In the photoreceptor of FIG. 4, a charge generation layer (35) mainly composed of a charge generation material and a charge transport layer (37) mainly composed of a charge transport material are laminated on a conductive support (31). Further, a protective layer (39) is provided on the charge transport layer.
In the photoreceptor of FIG. 5, a charge transport layer (37) mainly composed of a charge transport material and a charge generation layer (35) mainly composed of a charge generation material are laminated on a conductive support (31). Further, a protective layer (39) is provided on the charge generation layer.
The triphenylene derivatives represented by the general formulas (1) to (3) of the present invention are contained in the photosensitive layer of the photoreceptor shown in FIGS. 1 to 5, for example, in a layer containing a charge transport material. In the case where the protective layer (39) shown in FIGS. 3 to 5 is provided, it can also be contained in the protective layer.

As the conductive support (31), a material having a volume resistance of 10 ¹⁰ Ω · cm or less, for example, a metal such as aluminum, nickel, chromium, nichrome, copper, gold, silver, platinum, tin oxide, oxidation Metal oxide such as indium by vapor deposition or sputtering, film or cylindrical plastic, paper coated, or aluminum, aluminum alloy, nickel, stainless steel plates, etc. and methods such as extrusion and drawing After forming the tube, it is possible to use a tube subjected to surface treatment such as cutting, superfinishing or polishing. Further, an endless nickel belt and an endless stainless steel belt disclosed in Japanese Patent Application Laid-Open No. 52-36016 can be used as the conductive support (31).

  In addition, the conductive support dispersed in a suitable binder resin and coated on the support can also be used as the conductive support (31) of the present invention. Examples of the conductive powder include carbon black, acetylene black, metal powder such as aluminum, nickel, iron, nichrome, copper, zinc and silver, or metal oxide powder such as conductive tin oxide and ITO. It is done. The binder resin used at the same time is polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer. , Polyvinyl acetate, polyvinylidene chloride, polyarylate resin, phenoxy resin, polycarbonate, cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyl toluene, poly-N-vinyl carbazole, acrylic resin, silicone resin, epoxy resin, Examples thereof include thermoplastic, thermosetting resins, and photocurable resins such as melamine resin, urethane resin, phenol resin, and alkyd resin. Such a conductive layer can be provided by dispersing and coating these conductive powder and binder resin in a suitable solvent such as tetrahydrofuran, dichloromethane, methyl ethyl ketone, and toluene.

  Furthermore, it is electrically conductive by a heat-shrinkable tube in which the conductive powder is contained in a material such as polyvinyl chloride, polypropylene, polyester, polystyrene, polyvinylidene chloride, polyethylene, chlorinated rubber, Teflon (registered trademark) on a suitable cylindrical substrate. Those provided with a conductive layer can also be used favorably as the conductive support (31) of the present invention.

Next, the photosensitive layer will be described. The photosensitive layer may be a single layer or a laminate. For convenience of explanation, the photosensitive layer is first described from the case where it is composed of a charge generation layer (35) and a charge transport layer (37).
The charge generation layer (35) is a layer mainly composed of a charge generation material. A known charge generation material can be used for the charge generation layer (35), and representative examples thereof include CI Pigment Blue 25 (Color Index CI 21180), CI Pigment Red 41 (CI 21200), and CI Acid Red 52. (CI 45100), CI Basic Red 3 (CI 45210), azo pigments having a carbazole skeleton (described in JP-A-53-95033), azo pigments having a distyrylbenzene skeleton (JP-A-53-133445) ), An azo pigment having a triphenylamine skeleton (described in JP-A-53-132347), an azo pigment having a dibenzothiophene skeleton (described in JP-A-54-21728), an azo pigment having an oxadiazole skeleton Pigment (described in JP 54-12742 A) ), An azo pigment having a fluorenone skeleton (described in JP-A-54-22834), an azo pigment having a bis-stilbene skeleton (described in JP-A-54-17733), and a distyryloxadiazole skeleton Azo pigments such as azo pigments (described in JP-A No. 54-2129), azo pigments having a distyrylcarbazole skeleton (described in JP-A No. 54-14967), and azo pigments having a benzanthrone skeleton. For example, CI Pigment Blue 16 (CI 74100), Y-type oxotitanium phthalocyanine (Japanese Unexamined Patent Publication No. 64-17066), A (β) -type oxotitanium phthalocyanine, B (α) -type oxotitanium phthalocyanine, I-type oxotitanium phthalocyanine (Described in JP-A-11-21466), type II chlorogallium phthalocyanine (Iijima et al., Chemical Society of Japan, 67th Spring Annual, 1B4, 04 (1994)), type V hydroxygallium phthalocyanine (Damon et al., Chemical Society of Japan) 67th Spring Annual, 1B4, 05 (1994)), phthalocyanine pigments such as X-type metal-free phthalocyanine (US Pat. No. 3,816,118), C-Ibat Brown 5 (CI 73410), C-Ibat Dye (CI) 7330) and other indigo pigments, Lugo (manufactured by Bayer Co., Ltd.) Scarlet B, such as perylene pigment, such as in-closet Ren Scarlet R (manufactured by Bayer Co., Ltd.) and the like. These materials may be used alone or in combination of two or more.

  In the charge generation layer (35), the charge generation material is dispersed in a suitable solvent together with a binder resin if necessary using a ball mill, attritor, sand mill, ultrasonic wave, etc., and this is applied onto the conductive support. And formed by drying.

  The binder resin used for the charge generation layer (35) as necessary may be polyamide, polyurethane, epoxy resin, polyketone, polycarbonate, silicone resin, acrylic resin, polyvinyl butyral, polyvinyl formal, polyvinyl ketone, polystyrene, polysulfone, poly -N-vinyl carbazole, polyacrylamide, polyvinyl benzal, polyester, phenoxy resin, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyphenylene oxide, polyamide, polyvinyl pyridine, cellulosic resin, casein, polyvinyl alcohol, polyvinyl pyrrolidone Etc. The amount of the binder resin is suitably 0 to 500 parts by weight, preferably 10 to 300 parts by weight with respect to 100 parts by weight of the charge generating material. The binder resin may be added before or after dispersion.

  Examples of the solvent used here include isopropanol, acetone, methyl ethyl ketone, cyclohexanone, tetrahydrofuran, dioxane, ethyl cellosolve, ethyl acetate, methyl acetate, dichloromethane, dichloroethane, monochlorobenzene, cyclohexane, toluene, xylene, and ligroin. In particular, ketone solvents, ester solvents, and ether solvents are preferably used. These may be used alone or in combination of two or more.

The charge generation layer (35) is mainly composed of a charge generation material, a solvent, and a binder resin, and includes any additive such as a sensitizer, a dispersant, a surfactant, and silicone oil. May be.
As a coating method of the coating solution, methods such as dip coating, spray coating, beat coating, nozzle coating, spinner coating, ring coating, and the like can be used.
The film thickness of the charge generation layer (35) is suitably about 0.01 to 5 μm, preferably 0.1 to 2 μm.

The charge transport layer (37) is a layer mainly composed of a charge transport material.
The charge transport material is divided into a hole transport material, an electron transport material, and a polymer charge transport material, which will be described below.
Examples of the hole transport material include poly-N-carbazole and derivatives thereof, poly-γ-carbazolylethyl glutamate and derivatives thereof, pyrene-formaldehyde condensates and derivatives thereof, polyvinylpyrene, polyvinylphenanthrene, oxazole derivatives, imidazole There are derivatives, triphenylamine derivatives, and compounds represented by the general formula:

（式中、Ｒ^１はメチル基、エチル基、２−ヒドロキシエチル基または２−クロルエチル基を表わし、Ｒ^２はメチル基、エチル基、ベンジル基またはフェニル基を表わし、Ｒ^３は水素原子、塩素原子、臭素原子、炭素数１〜４のアルキル基、炭素数１〜４のアルコキシ基、ジアルキルアミノ基またはニトロ基を表わす。）

(Wherein R ¹ represents a methyl group, an ethyl group, a 2-hydroxyethyl group or a 2-chloroethyl group, R ² represents a methyl group, an ethyl group, a benzyl group or a phenyl group, and R ³ represents a hydrogen atom, chlorine An atom, a bromine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a dialkylamino group, or a nitro group.)

（式中、Ａｒはナフタレン環、アントラセン環、ピレン環及びそれらの置換体あるいはピリジン環、フラン環、チオフェン環を表わし、Ｒはアルキル基、フェニル基またはベンジル基を表わす。）

(In the formula, Ar represents a naphthalene ring, anthracene ring, pyrene ring and a substituted product thereof, or a pyridine ring, a furan ring, and a thiophene ring, and R represents an alkyl group, a phenyl group, or a benzyl group.)

（式中、Ｒ^１はアルキル基、ベンジル基、フェニル基またはナフチル基を表わし、Ｒ^２は水素原子、炭素数１〜３のアルキル基、炭素数１〜３のアルコキシ基、ジアルキルアミノ基、ジアラルキルアミノ基、または置換もしくは無置換のジアリールアミノ基を表わし、ｎは１〜４の整数を表わし、ｎが２以上のときはＲ^２は同じでも異なっていても良い。Ｒ^３は水素原子またはメトキシ基を表わす。）

(Wherein R ¹ represents an alkyl group, a benzyl group, a phenyl group or a naphthyl group, and R ² represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a dialkylamino group, a dialkyl group) Represents an aralkylamino group or a substituted or unsubstituted diarylamino group, n represents an integer of 1 to 4, and when n is 2 or more, R ² may be the same or different, and R ³ represents a hydrogen atom or Represents a methoxy group.)

（式中、Ｒ^１は炭素数１〜１１のアルキル基、置換もしくは無置換のフェニル基または複素環基を表わし、Ｒ^２、Ｒ^３はそれぞれ同一でも異なっていてもよく、水素原子、炭素数１〜４のアルキル基、ヒドロキシアルキル基、クロルアルキル基または置換もしくは無置換のアラルキル基を表わし、また、Ｒ^２とＲ^３は互いに結合し窒素を含む複素環を形成していても良い。Ｒ^４は同一でも異なっていてもよく、水素原子、炭素数１〜４のアルキル基、アルコキシ基またはハロゲン原子を表わす。）

(In the formula, R ¹ represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group or a heterocyclic group, and R ² and R ³ may be the same or different, and each represents a hydrogen atom or a carbon number. Represents an alkyl group of 1-4, a hydroxyalkyl group, a chloroalkyl group, or a substituted or unsubstituted aralkyl group, and R ² and R ³ may be bonded to each other to form a nitrogen-containing heterocyclic ring. ⁴ may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group or a halogen atom.

（式中、Ｒは水素原子またはハロゲン原子を表わし、Ａｒは置換もしくは無置換のフェニル基、ナフチル基、アントリル基またはカルバゾリル基を表わす。）

(In the formula, R represents a hydrogen atom or a halogen atom, and Ar represents a substituted or unsubstituted phenyl group, naphthyl group, anthryl group or carbazolyl group.)

（式中、Ｒ^１は水素原子、ハロゲン原子、シアノ基、炭素数１〜４のアルコキシ基または炭素数１〜４のアルキル基を表わし、Ａｒは

(Wherein R ¹ represents a hydrogen atom, a halogen atom, a cyano group, an alkoxy group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms;

を表わし、Ｒ^２は炭素数１〜４のアルキル基を表わし、Ｒ^３は水素原子、ハロゲン原子、炭素数１〜４のアルキル基、炭素数１〜４のアルコキシ基またはジアルキルアミノ基を表わし、ｎは１または２であって、ｎが２のときはＲ^３は同一でも異なっていてもよく、Ｒ^４、Ｒ^５は水素原子、炭素数１〜４の置換もしくは無置換のアルキル基または置換もしくは無置換のベンジル基を表わす。）

R ² represents an alkyl group having 1 to 4 carbon atoms, R ³ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a dialkylamino group, n is 1 or 2, and when n is 2, R ³ may be the same or different, and R ⁴ and R ⁵ are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted group. Alternatively, it represents an unsubstituted benzyl group. )

（式中、Ｒはカルバゾリル基、ピリジル基、チエニル基、インドリル基、フリル基あるいはそれぞれ置換もしくは非置換のフェニル基、スチリル基、ナフチル基、またはアントリル基であって、これらの置換基がジアルキルアミノ基、アルキル基、アルコキシ基、カルボキシ基またはそのエステル、ハロゲン原子、シアノ基、アラルキルアミノ基、Ｎ−アルキル−Ｎ−アラルキルアミノ基、アミノ基、ニトロ基及びアセチルアミノ基からなる群から選ばれた基を表わす。）

Wherein R is a carbazolyl group, pyridyl group, thienyl group, indolyl group, furyl group or a substituted or unsubstituted phenyl group, styryl group, naphthyl group, or anthryl group, and these substituents are dialkylamino Group, alkyl group, alkoxy group, carboxy group or ester thereof, halogen atom, cyano group, aralkylamino group, N-alkyl-N-aralkylamino group, amino group, nitro group, and acetylamino group Represents a group.)

（式中、Ｒ^１は低級アルキル基、置換もしくは無置換のフェニル基、またはベンジル基を表わし、Ｒ^２、Ｒ^３は水素原子、低級アルキル基、低級アルコキシ基、ハロゲン原子、ニトロ基、アミノ基あるいは低級アルキル基またはベンジル基で置換されたアミノ基を表わし、ｎは１または２の整数を表わす。）

(In the formula, R ¹ represents a lower alkyl group, a substituted or unsubstituted phenyl group, or a benzyl group, and R ² and R ³ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, and an amino group. Alternatively, it represents an amino group substituted with a lower alkyl group or a benzyl group, and n represents an integer of 1 or 2.)

（式中、Ｒ^１は水素原子、アルキル基、アルコキシ基またはハロゲン原子を表わし、Ｒ^２およびＲ^３は置換もしくは無置換のアリール基を表わし、Ｒ^４は水素原子、低級アルキル基または置換もしくは無置換のフェニル基を表わし、また、Ａｒは置換もしくは無置換のフェニル基またはナフチル基を表わす。）

(In the formula, R ¹ represents a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, R ² and R ³ represent a substituted or unsubstituted aryl group, and R ⁴ represents a hydrogen atom, a lower alkyl group or a substituted or unsubstituted group. Represents a substituted phenyl group, and Ar represents a substituted or unsubstituted phenyl group or a naphthyl group.)

〔式中、ｎは０または１の整数、Ｒ^１は水素原子、アルキル基または置換もしくは無置換のフェニル基を表わし、Ａｒ^１は置換もしくは無置換の芳香族炭化水素環基を表わし、Ｒ^５は炭素数１〜４アルキル基、あるいは置換もしくは無置換の芳香族炭化水素環基を表わし、Ａｒ^１とＲ^５は共同で環を形成しても良い。Ａは式

[Wherein n represents an integer of 0 or 1, R ¹ represents a hydrogen atom, an alkyl group, or a substituted or unsubstituted phenyl group, Ar ¹ represents a substituted or unsubstituted aromatic hydrocarbon ring group, R ⁵ Represents an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring group, and Ar ¹ and R ⁵ may jointly form a ring. A is an expression

あるいは

Or

で表される置換基、
｛但し、上記式中Ｒ^２は水素原子、アルキル基、アルコキシ基、ハロゲン原子または式

A substituent represented by
{Wherein R ² is a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or a formula

（ただし、Ｒ^３およびＲ^４は置換もしくは無置換の芳香族炭化水素環基を示し、Ｒ^３およびＲ^４は同じでも異なっていてもよく、環を形成しても良い）を表わし、ｍは１〜３の整数を表わし、２以上のときＲ^２は同一でも異なっても良い。｝
９−アントリル基または置換もしくは無置換のカルバゾリル基を表わす。また、ｎが０のとき、ＡとＲ^１は共同で環を形成しても良い。〕

Wherein R ³ and R ⁴ represent a substituted or unsubstituted aromatic hydrocarbon ring group, and R ³ and R ⁴ may be the same or different and may form a ring, and m represents Represents an integer of 1 to 3, and R ² may be the same or different when it is 2 or more. }
It represents a 9-anthryl group or a substituted or unsubstituted carbazolyl group. When n is 0, A and R ¹ may form a ring together. ]

（式中、Ｒ^１、Ｒ^２およびＲ^３は水素原子、低級アルキル基、低級アルコキシ基、ハロゲン原子またはジアルキルアミノ基を表わし、ｎは０または１を表わす。）

(Wherein R ¹ , R ² and R ³ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a dialkylamino group, and n represents 0 or 1)

（式中、Ｒ^１およびＲ^２は置換アルキル基を含むアルキル基、または置換もしくは未置換のアリール基を表わし、Ａは置換アミノ基、置換もしくは未置換のアリール基またはアリル基を表わす。）

(Wherein R ¹ and R ² represent an alkyl group including a substituted alkyl group, or a substituted or unsubstituted aryl group, and A represents a substituted amino group, a substituted or unsubstituted aryl group, or an allyl group.)

（式中、Ｘは水素原子、低級アルキル基またはハロゲン原子を表わし、Ｒは置換アルキル基を含むアルキル基、または置換もしくは無置換のアリール基を表わし、Ａは置換アミノ基または置換もしくは無置換のアリール基を表わす。）

(In the formula, X represents a hydrogen atom, a lower alkyl group or a halogen atom, R represents an alkyl group containing a substituted alkyl group, or a substituted or unsubstituted aryl group, and A represents a substituted amino group or a substituted or unsubstituted aryl group. Represents an aryl group.)

（式中、Ｒ^１は低級アルキル基、低級アルコキシ基またはハロゲン原子を表わし、Ｒ^２、Ｒ^３は同じでも異なっていてもよく、水素原子、低級アルキル基、低級アルコキシ基またはハロゲン原子を表わし、ｌ、ｍ、ｎは０〜４の整数を表わす。）

(Wherein R ¹ represents a lower alkyl group, a lower alkoxy group or a halogen atom, R ² and R ³ may be the same or different, and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; l, m, and n represent an integer of 0 to 4.)

（式中、Ｒ^１、Ｒ^３およびＲ^４は水素原子、アミノ基、アルコキシ基、チオアルコキシ基、アリールオキシ基、メチレンジオキシ基、置換もしくは無置換のアルキル基、ハロゲン原子または置換もしくは無置換のアリール基を、Ｒ^２は水素原子、アルコキシ基、置換もしくは無置換のアルキル基またはハロゲン原子を表わす。また、ｋ，ｌ，ｍおよびｎは１、２、３または４の整数であり、それぞれが２、３または４の整数のときは、前記Ｒ^１、Ｒ^２、Ｒ^３およびＲ^４は同じでも異なっていても良い。）

(Wherein R ¹ , R ³ and R ⁴ are a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted group. R ² represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, and k, l, m and n are integers of 1, 2, 3 or 4, When R is an integer of 2, 3 or 4, the R ¹ , R ² , R ³ and R ⁴ may be the same or different.)

（式中、Ａｒは置換基を有してもよい炭素数１８個以下の縮合多環式炭化水素基を表わし、また、Ｒ^１およびＲ^２は水素原子、ハロゲン原子、置換もしくは無置換のアルキル基、アルコキシ基、置換もしくは無置換のフェニル基を表わし、それぞれ同じでも異なっていても良い。ｎは１もしくは２の整数を表わす。）

(In the formula, Ar represents a condensed polycyclic hydrocarbon group having 18 or less carbon atoms which may have a substituent, and R ¹ and R ² are a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group. A group, an alkoxy group, a substituted or unsubstituted phenyl group, which may be the same or different, and n represents an integer of 1 or 2.)

（式中、Ａｒは置換もしくは無置換の芳香族炭化水素基を表わし、Ａは

(In the formula, Ar represents a substituted or unsubstituted aromatic hydrocarbon group, and A represents

（ただし、Ａｒ'は置換もしくは無置換の芳香族炭化水素基を表わし、Ｒ^１およびＲ^２は置換もしくは無置換のアルキル基、または置換もしくは無置換のアリール基である。）を表わす。）

(Wherein Ar ′ represents a substituted or unsubstituted aromatic hydrocarbon group, and R ¹ and R ² represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group). )

（式中、Ａｒは置換もしくは無置換の芳香族炭化水素基を、Ｒは水素原子、置換もしくは無置換のアルキル基、または置換もしくは無置換のアリール基を表わす。ｎは０または１、ｍは１または２であって、ｎ＝０、ｍ＝１の場合、ＡｒとＲは共同で環を形成しても良い。）

(In the formula, Ar represents a substituted or unsubstituted aromatic hydrocarbon group, R represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. N is 0 or 1, m is When 1 or 2 and n = 0 and m = 1, Ar and R may form a ring together.)

Examples of the compound represented by the general formula (11) include 9-ethylcarbazole-3-aldehyde-1-methyl-1-phenylhydrazone, 9-ethylcarbazole-3-aldehyde-1-benzyl-1-phenylhydrazone. 9-ethylcarbazole-3-aldehyde-1,1-diphenylhydrazone.
Examples of the compound represented by the general formula (12) include 4-diethylaminostyryl-β-aldehyde-1-methyl-1-phenylhydrazone, 4-methoxynaphthalene-1-aldehyde-1-benzyl-1- There is phenyl hydrazone.
Examples of the compound represented by the general formula (13) include 4-methoxybenzaldehyde-1-methyl-1-phenylhydrazone, 2,4-dimethoxybenzaldehyde-1-benzyl-1-phenylhydrazone, 4-diethylaminobenzaldehyde- 1,1-diphenylhydrazone, 4-methoxybenzaldehyde-1- (4-methoxy) phenylhydrazone, 4-diphenylaminobenzaldehyde-1-benzyl-1-phenylhydrazone, 4-dibenzylaminobenzaldehyde-1,1-diphenylhydrazone and so on.
Examples of the compound represented by the general formula (14) include 1,1-bis (4-dibenzylaminophenyl) propane, tris (4-diethylaminophenyl) methane, 1,1-bis (4-di-). Benzylaminophenyl) propane, 2,2′-dimethyl-4,4′-bis (diethylamino) -triphenylmethane, and the like.
Examples of the compound represented by the general formula (15) include 9- (4-diethylaminostyryl) anthracene and 9-bromo-10- (4-diethylaminostyryl) anthracene.
Examples of the compound represented by the general formula (16) include 9- (4-dimethylaminobenzylidene) fluorene and 3- (9-fluorenylidene) -9-ethylcarbazole.
Examples of the compound represented by the general formula (17) include 1,2-bis (4-diethylaminostyryl) benzene and 1,2-bis (2,4-dimethoxystyryl) benzene.
Examples of the compound represented by the general formula (18) include 3-styryl-9-ethylcarbazole and 3- (4-methoxystyryl) -9-ethylcarbazole.
Examples of the compound represented by the general formula (19) include 4-diphenylaminostilbene, 4-dibenzylaminostilbene, 4-ditolylaminostilbene, 1- (4-diphenylaminostyryl) naphthalene, 1- (4 -Diphenylaminostyryl) naphthalene.
Examples of the compound represented by the general formula (20) include 4′-diphenylamino-α-phenylstilbene and 4′-bis (4-methylphenyl) amino-α-phenylstilbene.
Examples of the compound represented by the general formula (21) include 1-phenyl-3- (4-diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazoline.
Examples of the compound represented by the general formula (22) include 2,5-bis (4-diethylaminophenyl) -1,3,4-oxadiazole, 2-N, N-diphenylamino-5- (4 -Diethylaminophenyl) -1,3,4-oxadiazole, 2- (4-dimethylaminophenyl) -5- (4-diethylaminophenyl) -1,3,4-oxadiazole and the like.
Examples of the compound represented by the general formula (23) include 2-N, N-diphenylamino-5- (N-ethylcarbazol-3-yl) -1,3,4-oxadiazole, 2- ( 4-diethylaminophenyl) -5- (N-ethylcarbazol-3-yl) -1,3,4-oxadiazole.
Examples of the benzidine compound represented by the general formula (24) include N, N′-diphenyl-N, N′-bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-. Examples include diamine, 3,3′-dimethyl-N, N, N ′, N′-tetrakis (4-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine.
Examples of the biphenylylamine compound represented by the general formula (25) include 4′-methoxy-N, N-diphenyl- [1,1′-biphenyl] -4-amine and 4′-methyl-N. , N-bis (4-methylphenyl)-[1,1′-biphenyl] -4-amine, 4′-methoxy-N, N-bis (4-methylphenyl)-[1,1′-biphenyl]- 4-amine, N, N-bis (3,4-dimethylphenyl)-[1,1′-biphenyl] -4-amine and the like.
Examples of the triarylamine compound represented by the general formula (26) include N, N-diphenyl-pyrene-1-amine, N, N-di-p-tolyl-pyrene-1-amine, N, N-di-p-tolyl-1-naphthylamine, N, N-di (p-tolyl) -1-phenanthrylamine, 9,9-dimethyl-2- (di-p-tolylamino) fluorene, N, N , N ′, N′-tetrakis (4-methylphenyl) -phenanthrene-9,10-diamine, N, N, N ′, N′-tetrakis (3-methylphenyl) -m-phenylenediamine, and the like.
Examples of the diolefin aromatic compound represented by the general formula (27) include 1,4-bis (4-diphenylaminostyryl) benzene and 1,4-bis [4-di (p-tolyl) amino. Styryl] benzene.
Examples of the styrylpyrene compound represented by the general formula (28) include 1- (4-diphenylaminostyryl) pyrene and 1- (N, N-di-p-tolyl-4-aminostyryl) pyrene. .

  Examples of the electron transport material include chloroanil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone, 2,4,5,7-tetranitro-9-fluorenone, 2,4,5,7-tetranitroxanthone, 2,4,8-trinitrothioxanthone, 2,6,8-trinitro-indeno4H-indeno [1,2-b] thiophen-4-one, 1,3 , 7-trinitrodibenzothiophene-5,5-dioxide and the like, and the electron transport materials listed in the following general formulas (29), (30) and (31) can be preferably used. These charge transport materials may be used alone or in combination of two or more.

（式中Ｒ^１、Ｒ^２およびＲ^３は水素原子、ハロゲン原子、置換もしくは無置換のアルキル基、アルコキシ基、置換もしくは無置換のフェニル基を表わし、それぞれ同じでも異なっていても良い。）

(Wherein R ¹ , R ² and R ³ represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group or a substituted or unsubstituted phenyl group, and may be the same or different.)

（式中Ｒ^１、Ｒ^２は水素原子、置換もしくは無置換のアルキル基、置換もしくは無置換のフェニル基を表わし、それぞれ同じでも異なっていても良い。）

(Wherein R ¹ and R ² represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group, and may be the same or different.)

（式中Ｒ^１、Ｒ^２およびＲ^３は水素原子、ハロゲン原子、置換もしくは無置換のアルキル基、アルコキシ基、置換もしくは無置換のフェニル基を表わし、それぞれ同じでも異なっていても良い。）

(Wherein R ¹ , R ² and R ³ represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group or a substituted or unsubstituted phenyl group, and may be the same or different.)

  As the binder resin, polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, Polyvinylidene chloride, polyarylate resin, phenoxy resin, polycarbonate, cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyl toluene, poly-N-vinyl carbazole, acrylic resin, silicone resin, epoxy resin, melamine resin, urethane resin And thermoplastic or thermosetting resins such as phenol resins and alkyd resins.

  When the charge transport material and the triphenylene derivative represented by the general formulas (1) to (3) of the present invention are mixed and contained in the charge transport layer, the total amount is 20 to 20 parts by weight with respect to 100 parts by weight of the binder resin. 300 parts by weight, preferably 40 to 150 parts by weight is suitable. The thickness of the charge transport layer is preferably 25 μm or less from the viewpoint of resolution and responsiveness. Regarding the lower limit, although it differs depending on the system to be used (particularly the charging potential), 5 μm or more is preferable.

  The amount of the triphenylene derivative represented by the general formulas (1) to (3) of the present invention is preferably 0.01 wt% to 150 wt% with respect to the charge transport material. If the amount is too small, the resistance to the oxidizing gas is insufficient. If the amount is too large, the residual potential increases greatly due to repeated use.

  As the solvent used here, tetrahydrofuran, dioxane, toluene, dichloromethane, monochlorobenzene, dichloroethane, cyclohexanone, methyl ethyl ketone, acetone and the like are used. The charge transport materials may be used alone or in combination of two or more.

  As the antioxidant that can be used in the present invention, a general antioxidant described later can be used, and (c) hydroquinone-based compounds and (f) hindered amine-based compounds are particularly effective. However, the antioxidant used here is used for the alteration protection of the amine compound of the present invention to the last, unlike the purpose described later. For this reason, these antioxidants are preferably contained in the coating liquid in the step before containing the amine compound of the present invention, and the addition amount is 0.1 to 200 wt% with respect to the amine compound. Can produce a sufficient effect.

  For the charge transport layer, a polymer charge transport material having a function as a charge transport material and a function as a binder resin is also preferably used. The charge transport layer composed of these polymer charge transport materials is excellent in wear resistance. As the polymer charge transport material, known materials can be used, and in particular, a polycarbonate containing a triarylamine structure in the main chain and / or side chain is preferably used. Among these, polymer charge transport materials represented by the formulas (I) to (XI) are preferably used. These are illustrated below and specific examples are shown.

式中、Ｒ_１，Ｒ_２，Ｒ_３はそれぞれ独立して置換もしくは無置換のアルキル基又はハロゲン原子、Ｒ_４は水素原子又は置換もしくは無置換のアルキル基、Ｒ_５，Ｒ_６は置換もしくは無置換のアリール基、ｏ，ｐ，ｑはそれぞれ独立して０〜４の整数、ｋ，ｊは組成を表わし、０．１≦ｋ≦１、０≦ｊ≦０．９、ｎは繰り返し単位数を表わし５〜５０００の整数である。Ｘは脂肪族の２価基、環状脂肪族の２価基、または下記一般式Ｓ１もしくはＳ２で表わされる２価基を表わす。

In the formula, R ₁ , R ₂ and R ₃ are each independently a substituted or unsubstituted alkyl group or a halogen atom, R ₄ is a hydrogen atom or a substituted or unsubstituted alkyl group, and R ₅ and R ₆ are substituted or unsubstituted. Substituted aryl group, o, p, q are each independently an integer of 0-4, k, j are compositions, 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n is the number of repeating units Represents an integer of 5 to 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula S1 or S2.

（但し、一般式Ｓ１中、Ｒ_１０１，Ｒ_１０２は各々独立して置換もしくは無置換のアルキル基、芳香環基またはハロゲン原子を表わす。ｌ、ｍは０〜４の整数、Ｙは単結合、炭素原子数１〜１２の直鎖状、分岐状もしくは環状のアルキレン基、−Ｏ−，−Ｓ−，−ＳＯ−，−ＳＯ_２−，−ＣＯ−，−ＣＯ−Ｏ−Ｚ−Ｏ−ＣＯ−（式中Ｚは脂肪族の２価基を表わす。）を表わし、一般式Ｓ２中、ａは１〜２０の整数、ｂは１〜２０００の整数、Ｒ_１０３、Ｒ_１０４は置換または無置換のアルキル基又はアリール基を表わす。）ここで、Ｒ_１０１とＲ_１０２，Ｒ_１０３とＲ_１０４は、それぞれ同一でも異なってもよい。）を表わす。〕

(In the general formula S1, R ₁₀₁ and R ₁₀₂ each independently represents a substituted or unsubstituted alkyl group, an aromatic ring group or a halogen atom. L, m are integers of 0 to 4, Y is a single bond, A linear, branched or cyclic alkylene group having 1 to 12 carbon atoms, —O—, —S—, —SO—, —SO ₂ —, —CO—, —CO—O—Z—O—CO -(Wherein Z represents an aliphatic divalent group), in general formula S2, a is an integer of 1 to 20, b is an integer of 1 to 2000, and R ₁₀₃ and R ₁₀₄ are substituted or unsubstituted. R ₁₀₁ and R ₁₀₂ , R ₁₀₃ and R ₁₀₄ may be the same or different from each other. ). ]

式中、Ｒ_７，Ｒ_８は置換もしくは無置換のアリール基、Ａｒ_１，Ａｒ_２，Ａｒ_３は同一あるいは異なるアリレン基を表わす。Ｘ，ｋ，ｊおよびｎは、（Ｉ）式の場合と同じである。

In the formula, R ₇ and R ₈ represent substituted or unsubstituted aryl groups, and Ar ₁ , Ar ₂ , and Ar ₃ represent the same or different arylene groups. X, k, j and n are the same as in the case of formula (I).

式中、Ｒ_９，Ｒ_１０は置換もしくは無置換のアリール基、Ａｒ_４，Ａｒ_５，Ａｒ_６は同一あるいは異なるアリレン基を表わす。Ｘ，ｋ，ｊおよびｎは、（Ｉ）式の場合と同じである。

In the formula, R ₉ and R ₁₀ represent a substituted or unsubstituted aryl group, and Ar ₄ , Ar ₅ , and Ar ₆ represent the same or different arylene groups. X, k, j and n are the same as in the case of formula (I).

式中、Ｒ_１１，Ｒ_１２は置換もしくは無置換のアリール基、Ａｒ_７，Ａｒ_８，Ａｒ_９は同一あるいは異なるアリレン基、ｐは１〜５の整数を表わす。Ｘ，ｋ，ｊおよびｎは、（Ｉ）式の場合と同じである。

In the formula, R ₁₁ and R ₁₂ are substituted or unsubstituted aryl groups, Ar ₇ , Ar ₈ and Ar ₉ are the same or different arylene groups, and p represents an integer of 1 to 5. X, k, j and n are the same as in the case of formula (I).

式中、Ｒ_１３，Ｒ_１４は置換もしくは無置換のアリール基、Ａｒ_１０，Ａｒ_１１，Ａｒ_１２は同一あるいは異なるアリレン基、Ｘ_１，Ｘ_２は置換もしくは無置換のエチレン基、又は置換もしくは無置換のビニレン基を表わす。Ｘ，ｋ，ｊおよびｎは、（Ｉ）式の場合と同じである。

In the formula, R ₁₃ and R ₁₄ are substituted or unsubstituted aryl groups, Ar ₁₀ , Ar ₁₁ and Ar ₁₂ are the same or different arylene groups, X ₁ and X ₂ are substituted or unsubstituted ethylene groups, or substituted or unsubstituted Represents a substituted vinylene group. X, k, j and n are the same as in the case of formula (I).

式中、Ｒ_１５，Ｒ_１６，Ｒ_１７，Ｒ_１８は置換もしくは無置換のアリール基、Ａｒ_１３，Ａｒ_１４，Ａｒ_１５，Ａｒ_１６は同一あるいは異なるアリレン基、Ｙ_１，Ｙ_２，Ｙ_３は単結合、置換もしくは無置換のアルキレン基、置換もしくは無置換のシクロアルキレン基、置換もしくは無置換のアルキレンエーテル基、酸素原子、硫黄原子、ビニレン基を表わし同一であっても異なってもよい。Ｘ，ｋ，ｊおよびｎは、（Ｉ）式の場合と同じである。

In the formula, R ₁₅ , R ₁₆ , R ₁₇ and R ₁₈ are substituted or unsubstituted aryl groups, Ar ₁₃ , Ar ₁₄ , Ar ₁₅ and Ar ₁₆ are the same or different arylene groups, and Y ₁ , Y ₂ and Y ₃ are A single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene ether group, an oxygen atom, a sulfur atom, or a vinylene group may be the same or different. X, k, j and n are the same as in the case of formula (I).

式中、Ｒ_１９，Ｒ_２０は水素原子、置換もしくは無置換のアリール基を表わし，Ｒ_１９とＲ_２０は環を形成していてもよい。Ａｒ_１７，Ａｒ_１８，Ａｒ_１９は同一あるいは異なるアリレン基を表わす。Ｘ，ｋ，ｊおよびｎは、（Ｉ）式の場合と同じである。

In the formula, R ₁₉ and R _{20 each} represent a hydrogen atom or a substituted or unsubstituted aryl group, and R ₁₉ and R ₂₀ may form a ring. Ar ₁₇ , Ar ₁₈ and Ar ₁₉ represent the same or different arylene groups. X, k, j and n are the same as in the case of formula (I).

式中、Ｒ_２１は置換もしくは無置換のアリール基、Ａｒ_２０，Ａｒ_２１，Ａｒ_２２，Ａｒ_２３は同一あるいは異なるアリレン基を表わす。Ｘ，ｋ，ｊおよびｎは、（Ｉ）式の場合と同じである。

In the formula, R ₂₁ represents a substituted or unsubstituted aryl group, and Ar ₂₀ , Ar ₂₁ , Ar ₂₂ , and Ar ₂₃ represent the same or different arylene groups. X, k, j and n are the same as in the case of formula (I).

式中、Ｒ_２２，Ｒ_２３，Ｒ_２４，Ｒ_２５は置換もしくは無置換のアリール基、Ａｒ_２４，Ａｒ_２５，Ａｒ_２６，Ａｒ_２７，Ａｒ_２８は同一あるいは又は異なるアリレン基を表わす。Ｘ，ｋ，ｊおよびｎは、（Ｉ）式の場合と同じである。

In the formula, R ₂₂ , R ₂₃ , R ₂₄ and R ₂₅ represent a substituted or unsubstituted aryl group, and Ar ₂₄ , Ar ₂₅ , Ar ₂₆ , Ar ₂₇ and Ar ₂₈ represent the same or different arylene groups. X, k, j and n are the same as in the case of formula (I).

式中、Ｒ_２６，Ｒ_２７は置換もしくは無置換のアリール基、Ａｒ_２９，Ａｒ_３０，Ａｒ_３１は同一あるいは異なるアリレン基を表わす。Ｘ，ｋ，ｊおよびｎは、（Ｉ）式の場合と同じである。

In the formula, R ₂₆ and R ₂₇ represent a substituted or unsubstituted aryl group, and Ar ₂₉ , Ar ₃₀ and Ar ₃₁ represent the same or different arylene groups. X, k, j and n are the same as in the case of formula (I).

（式中、Ａｒ_１、Ａｒ_２、Ａｒ_３、Ａｒ_４およびＡｒ_５は置換もしくは無置換の芳香環基、Ｚは芳香環基または―Ａｒ_６―Ｚａ―Ａｒ_６―を表わし、Ａｒ_６は置換もしくは無置換の芳香環基、ＺａはＯ、Ｓまたはアルキレン基、ＲおよびＲ'は直鎖又は分岐鎖のアルキレン基を表わす。ｍは０または１を表わす。Ｘ，ｋ，ｊおよびｎは、（Ｉ）式の場合と同じである。）

(In the formula, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ and Ar ₅ represent a substituted or unsubstituted aromatic ring group, Z represents an aromatic ring group or —Ar ₆ —Za—Ar ₆ —, and Ar ₆ represents a substituted group. Or an unsubstituted aromatic ring group, Za represents O, S or an alkylene group, R and R ′ represent a linear or branched alkylene group, m represents 0 or 1, and X, k, j and n represent (Same as in formula (I).)

  The charge transport layer (37) can be formed by dissolving or dispersing the charge transport material alone or in a binder resin and an appropriate solvent, and applying and drying the solution on the charge generation layer. Further, if necessary, two or more kinds of plasticizers, leveling agents, antioxidants and the like can be added.

  As a coating method of the coating liquid obtained as described above, conventional coating methods such as dip coating, spray coating, beat coating, nozzle coating, spinner coating, ring coating, and the like can be used.

  Next, the case where the photosensitive layer has a single layer configuration (33) will be described. A photoreceptor in which the above-described charge generating material is dispersed in a binder resin can be used. The photosensitive layer can be formed by dissolving or dispersing a charge generating substance, a charge transporting substance, and a binder resin in a suitable solvent, and applying and drying them. Moreover, a plasticizer, a leveling agent, antioxidant, etc. can also be added as needed.

  As the binder resin, in addition to the binder resin previously mentioned in the charge transport layer (37), the binder resin mentioned in the charge generation layer (35) may be mixed and used. Of course, the polymer charge transport materials mentioned above can also be used favorably. The amount of the charge generating material with respect to 100 parts by weight of the binder resin is preferably 5 to 40 parts by weight, and the amount of the charge transporting material is preferably 0 to 190 parts by weight, and more preferably 50 to 150 parts by weight. The photosensitive layer is formed by dip coating, spray coating, bead coating, a coating solution in which a charge generating material and a binder resin are dispersed together with a charge transporting material using a solvent such as tetrahydrofuran, dioxane, dichloroethane, and cyclohexane. It can be formed by coating with a ring coat or the like. The film thickness of the photosensitive layer is suitably about 5 to 25 μm.

  In the photoreceptor of the present invention, an undercoat layer can be provided between the conductive support (31) and the photosensitive layer. In general, the undercoat layer is mainly composed of a resin. However, considering that the photosensitive layer is coated with a solvent on these resins, the resin may be a resin having high solvent resistance with respect to a general organic solvent. desirable. Examples of such resins include water-soluble resins such as polyvinyl alcohol, casein, and sodium polyacrylate, alcohol-soluble resins such as copolymer nylon and methoxymethylated nylon, polyurethane, melamine resin, phenol resin, alkyd-melamine resin, and epoxy. Examples thereof include a curable resin that forms a three-dimensional network structure such as a resin. Further, a metal oxide fine powder pigment exemplified by titanium oxide, silica, alumina, zirconium oxide, tin oxide, indium oxide and the like may be added to the undercoat layer in order to prevent moire and reduce residual potential.

These undercoat layers can be formed using an appropriate solvent and a coating method like the above-mentioned photosensitive layer. Furthermore, a silane coupling agent, a titanium coupling agent, a chromium coupling agent, or the like can be used as the undercoat layer of the present invention. In addition, in the undercoat layer of the present invention, Al ₂ O ₃ is provided by anodic oxidation, organic matter such as polyparaxylylene (parylene), SiO ₂ , SnO ₂ , TiO ₂ , ITO, CeO ₂ A material provided with an inorganic material such as a vacuum thin film can also be used favorably. In addition, known ones can be used. The thickness of the undercoat layer is suitably from 0 to 5 μm.

  In the photoreceptor of the present invention, a protective layer (39) may be provided on the photosensitive layer for the purpose of protecting the photosensitive layer. Materials used for the protective layer (39) include ABS resin, ACS resin, olefin-vinyl monomer copolymer, chlorinated polyether, aryl resin, phenol resin, polyacetal, polyamide, polyamideimide, polyacrylate, polyallylsulfone. , Polybutylene, polybutylene terephthalate, polycarbonate, polyethersulfone, polyethylene, polyethylene terephthalate, polyimide, acrylic resin, polymethylbenten, polypropylene, polyphenylene oxide, polysulfone, polystyrene, polyarylate, AS resin, butadiene-styrene copolymer, polyurethane , Resins such as polyvinyl chloride, polyvinylidene chloride, and epoxy resin. From the viewpoint of filler dispersibility, residual potential, and coating film defects, polycarbonate or polyarylate is particularly effective and useful.

A filler material is added to the protective layer of the photoreceptor for the purpose of improving the wear resistance.
As a solvent to be used, a solvent used in the charge transport layer (37) such as tetrahydrofuran, dioxane, toluene, dichloromethane, monochlorobenzene, dichloroethane, cyclohexanone, methyl ethyl ketone, and acetone can be used. However, a solvent having a high viscosity is preferable at the time of dispersion, but a solvent having high volatility is preferable at the time of coating. When there is no solvent satisfying these conditions, it is possible to use a mixture of two or more solvents having respective physical properties, which may have a great effect on filler dispersibility and residual potential. .

Further, the protective layer may contain a triphenylene derivative represented by the general formulas (1) to (3) of the present invention. Furthermore, the addition of the low molecular charge transport material or the polymer charge transport material mentioned in the charge transport layer (37) is effective and useful for reducing the residual potential and improving the image quality.
As a method for forming the protective layer, conventional methods such as dip coating, spray coating, beat coating, nozzle coating, spinner coating, ring coating, etc. can be used. preferable.

  In the photoreceptor of the present invention, an intermediate layer can be provided between the photosensitive layer and the protective layer. In the intermediate layer, a binder resin is generally used as a main component. Examples of these resins include polyamide, alcohol-soluble nylon, water-soluble polyvinyl butyral, polyvinyl butyral, and polyvinyl alcohol. As a method for forming the intermediate layer, a generally used coating method as described above is employed. In addition, about 0.05-2 micrometers is suitable for the thickness of an intermediate | middle layer.

In the present invention, in order to improve environmental resistance, in order to prevent a decrease in sensitivity and an increase in residual potential, oxidation is performed on each layer such as a charge generation layer, a charge transport layer, an undercoat layer, a protective layer, and an intermediate layer. Inhibitors, plasticizers, lubricants, UV absorbers and leveling agents can be added. Representative materials of these compounds are described below.
Examples of the antioxidant that can be added to each layer include, but are not limited to, the following.
(A) Phenolic compounds 2,6-di-t-butyl-p-cresol, butylated hydroxyanisole, 2,6-di-t-butyl-4-ethylphenol, n-octadecyl-3- (4′- Hydroxy-3 ′, 5′-di-t-butylphenol), 2,2′-methylene-bis- (4-methyl-6-tert-butylphenol), 2,2′-methylene-bis- (4-ethyl-) 6-t-butylphenol), 4,4′-thiobis- (3-methyl-6-tert-butylphenol), 4,4′-butylidenebis- (3-methyl-6-tert-butylphenol), 1,1,3 -Tris- (2-methyl-4-hydroxy-5-t-butylphenyl) butane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxy Benzyl) benzene, te Lakis- [methylene-3- (3 ′, 5′-di-t-butyl-4′-hydroxyphenyl) propionate] methane, bis [3,3′-bis (4′-hydroxy-3′-t-butyl) Phenyl) butyric acid] cricol ester, tocopherols and the like.
(B) Paraphenylenediamines N-phenyl-N′-isopropyl-p-phenylenediamine, N, N′-di-sec-butyl-p-phenylenediamine, N-phenyl-N-sec-butyl-p-phenylene Diamine, N, N′-di-isopropyl-p-phenylenediamine, N, N′-dimethyl-N, N′-di-t-butyl-p-phenylenediamine and the like.
(C) Hydroquinones 2,5-di-t-octylhydroquinone, 2,6-didodecylhydroquinone, 2-dodecylhydroquinone, 2-dodecyl-5-chlorohydroquinone, 2-t-octyl-5-methylhydroquinone, 2 -(2-octadecenyl) -5-methylhydroquinone and the like.
(D) Organic sulfur compounds Dilauryl-3,3′-thiodipropionate, distearyl-3,3′-thiodipropionate, ditetradecyl-3,3′-thiodipropionate, and the like.
(E) Organic phosphorus compounds Triphenylphosphine, tri (nonylphenyl) phosphine, tri (dinonylphenyl) phosphine, tricresylphosphine, tri (2,4-dibutylphenoxy) phosphine and the like.

Examples of the plasticizer that can be added to each layer include, but are not limited to, the following.
(A) Phosphate ester plasticizer Triphenyl phosphate, tricresyl phosphate, trioctyl phosphate, octyl diphenyl phosphate, trichloroethyl phosphate, cresyl diphenyl phosphate, tributyl phosphate, tri-2-ethylhexyl phosphate, Triphenyl phosphate etc.
(B) Phthalate ester plasticizers Dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dibutyl phthalate, diheptyl phthalate, di-2-ethylhexyl phthalate, diisooctyl phthalate, di-n-octyl phthalate, phthalate Dinonyl acid, diisononyl phthalate, diisodecyl phthalate, diundecyl phthalate, ditridecyl phthalate, dicyclohexyl phthalate, butyl benzyl phthalate, butyl lauryl phthalate, methyl oleyl phthalate, octyl decyl phthalate, dibutyl fumarate, dioctyl fumarate Such.
(C) Aromatic carboxylic acid ester plasticizers Trioctyl trimellitic acid, tri-n-octyl trimellitic acid, octyl oxybenzoate, and the like.
(D) Aliphatic dibasic ester plasticizer dibutyl adipate, di-n-hexyl adipate, di-2-ethylhexyl adipate, di-n-octyl adipate, adipic acid n-octyl-n-decyl , Diisodecyl adipate, dicapryl adipate, di-2-ethylhexyl azelate, dimethyl sebacate, diethyl sebacate, dibutyl sebacate, di-n-octyl sebacate, di-2-ethylhexyl sebacate, di-2 sebacate -Ethoxyethyl, dioctyl succinate, diisodecyl succinate, dioctyl tetrahydrophthalate, di-n-octyl tetrahydrophthalate and the like.
(E) Fatty acid ester derivatives butyl oleate, glycerin monooleate, methyl acetylricinoleate, pentaerythritol ester, dipentaerythritol hexaester, triacetin, tributyrin and the like.
(F) Oxyacid ester plasticizers Methyl acetyl ricinoleate, butyl acetyl ricinoleate, butyl phthalyl butyl glycolate, tributyl acetyl citrate and the like.
(G) Epoxy plasticizer Epoxidized soybean oil, epoxidized linseed oil, butyl epoxy stearate, decyl epoxy stearate, octyl epoxy stearate, benzyl epoxy stearate, dioctyl epoxy hexahydrophthalate, didecyl epoxy hexahydrophthalate, etc. .
(H) Dihydric alcohol ester plasticizers such as diethylene glycol dibenzoate and triethylene glycol di-2-ethylbutyrate.
(I) Chlorinated plasticizer Chlorinated paraffin, chlorinated diphenyl, chlorinated fatty acid methyl, methoxychlorinated fatty acid methyl and the like.
(J) Polyester plasticizer Polypropylene adipate, polypropylene sebacate, polyester, acetylated polyester and the like.
(K) Sulfonic acid derivatives p-toluenesulfonamide, o-toluenesulfonamide, p-toluenesulfoneethylamide, o-toluenesulfoneethylamide, toluenesulfone-N-ethylamide, p-toluenesulfone-N-cyclohexylamide and the like.
(L) Citric acid derivatives Triethyl citrate, triethyl acetyl citrate, tributyl citrate, tributyl acetyl citrate, tri-2-ethylhexyl acetyl citrate, n-octyldecyl acetyl citrate and the like.
(M) Others Terphenyl, partially hydrogenated terphenyl, camphor, 2-nitrodiphenyl, dinonylnaphthalene, methyl abietate and the like.

Examples of the lubricant that can be added to each layer include, but are not limited to, the following.
(A) Hydrocarbon compound Liquid paraffin, paraffin wax, microwax, low-polymerized polyethylene and the like.
(B) Fatty acid compounds Lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid and the like.
(C) Fatty acid amide compounds Stearylamide, palmitylamide, oleinamide, methylenebisstearamide, ethylenebisstearamide and the like.
(D) Ester compounds Lower alcohol esters of fatty acids, polyhydric alcohol esters of fatty acids, fatty acid polyglycol esters, and the like.
(E) Alcohol compounds Cetyl alcohol, stearyl alcohol, ethylene glycol, polyethylene glycol, polyglycerol and the like.
(F) Metal soap Lead stearate, cadmium stearate, barium stearate, calcium stearate, zinc stearate, magnesium stearate and the like.
(G) Natural wax Carnauba wax, candelilla wax, beeswax, whale wax, ivotaro, montan wax and the like.
(H) Others Silicone compounds, fluorine compounds, etc.

Examples of the ultraviolet absorber that can be added to each layer include, but are not limited to, the following.
(A) Benzophenone series 2-hydroxybenzophenone, 2,4-dihydroxybenzophenone, 2,2 ′, 4-trihydroxybenzophenone, 2,2 ′, 4,4′-tetrahydroxybenzophenone, 2,2′-dihydroxy-4- Such as methoxybenzophenone.
(B) Salsylate type Phenyl salsylate, 2,4-di-t-butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate, and the like.
(C) Benzotriazole series (2′-hydroxyphenyl) benzotriazole, (2′-hydroxy5′-methylphenyl) benzotriazole, (2′-hydroxy5′-methylphenyl) benzotriazole, (2′-hydroxy3) '-Tert-butyl-5'-methylphenyl) 5-chlorobenzotriazole (d) cyanoacrylate series ethyl-2-cyano-3,3-diphenyl acrylate, methyl 2-carbomethoxy 3 (paramethoxy) acrylate, and the like.
(E) Quencher (metal complex)
Nickel (2,2′thiobis (4-t-octyl) phenolate) normal butylamine, nickel dibutyldithiocarbamate, nickel dibutyldithiocarbamate, cobalt dicyclohexyldithiophosphate and the like.
(F) HALS (hindered amine)
Bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, 1- [2- [3- (3 5-di-t-butyl-4-hydroxyphenyl) propionyloxy] ethyl] -4- [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionyloxy] -2,2,6 6-tetramethylpyridine, 8-benzyl-7,7,9,9-tetramethyl-3-octyl-1,3,8-triazaspiro [4,5] undecane-2,4-dione, 4-benzoyloxy- 2,2,6,6-tetramethylpiperidine and the like.

Next, the electrophotographic method and the electrophotographic apparatus of the present invention will be described in detail with reference to the drawings.
FIG. 6 is a schematic diagram for explaining the electrophotographic process and the electrophotographic apparatus of the present invention, and the following examples also belong to the category of the present invention.
In FIG. 6, the photoreceptor (1) is provided with at least a photosensitive layer, and the outermost surface layer contains a filler. The photosensitive member (1) has a drum shape, but may be a sheet or an endless belt. The charging charger (3), pre-transfer charger (7), transfer charger (10), separation charger (11), and pre-cleaning charger (13) include corotron, scorotron, solid state charger, and charging. A roller etc. are used and a well-known means can be used.
As the transfer means, the above charger can be generally used. However, as shown in the figure, a combination of the transfer charger (10) and the separation charger (11) is effective.
Further, light sources such as an image exposure unit (5) and a charge removal lamp (2) include fluorescent lamps, tungsten lamps, halogen lamps, mercury lamps, sodium lamps, light emitting diodes (LEDs), semiconductor lasers (LD), and electroluminescence (EL). ) And other luminescent materials can be used. Various types of filters such as a sharp cut filter, a band pass filter, a near infrared cut filter, a dichroic filter, an interference filter, and a color temperature conversion filter can be used to irradiate only light in a desired wavelength range.
In addition to the steps shown in FIG. 6, the light source and the like are provided with a transfer step, a static elimination step, a cleaning step, a pre-exposure step, and the like using light irradiation, so that the photosensitive member is irradiated with light.

  The toner developed on the photoconductor (1) by the developing unit (6) is transferred to the transfer paper (9), but not all is transferred and remains on the photoconductor (1). Toner is also produced. Such toner is removed from the photoreceptor by the fur brush (14) and the cleaning blade (15). Cleaning may be performed only with a cleaning brush, and a known brush such as a fur brush or a mag fur brush is used as the cleaning brush.

When the electrophotographic photosensitive member is positively (negatively) charged and image exposure is performed, a positive (negative) electrostatic latent image is formed on the surface of the photosensitive member. A positive image can be obtained by developing this with negative (positive) toner (electrodetection fine particles), and a negative image can be obtained by developing with positive (negative) toner.
A known method is applied to the developing unit, and a known method is also used for the charge eliminating unit.

  FIG. 7 shows another example of the electrophotographic process according to the present invention. The photosensitive member (21) has at least a photosensitive layer, and further contains a filler on the outermost surface layer. The photosensitive member (21) is driven by driving rollers (22a) and (22b) and charged by a charger (23), and a light source (24). Image exposure, development (not shown), transfer using a charger (25), pre-cleaning exposure using a light source (26), cleaning using a brush (27), and static elimination using a light source (28) are repeated. In FIG. 7, the photoconductor (21) (of course, the support is translucent in this case) is irradiated with pre-cleaning exposure light from the support side.

  The above illustrated electrophotographic process is illustrative of an embodiment of the present invention, and of course other embodiments are possible. For example, in FIG. 7, the pre-cleaning exposure is performed from the support side, but this may be performed from the photosensitive layer side, or image exposure and neutralization light irradiation may be performed from the support side.

  On the other hand, the light irradiation process is illustrated as image exposure, pre-cleaning exposure, and static elimination exposure. In addition, a pre-transfer exposure, a pre-exposure of image exposure, and other known light irradiation processes are provided to light the photosensitive member. Irradiation can also be performed.

  The image forming means as described above may be fixedly incorporated in a copying apparatus, a facsimile, or a printer, but may be incorporated in these apparatuses in the form of a process cartridge. A process cartridge is a single device (part) that contains a photosensitive member and includes a charging unit, an exposure unit, a developing unit, a transfer unit, a cleaning unit, and a charge eliminating unit. There are many shapes and the like of the process cartridge, but a general example is shown in FIG. The photoreceptor (16) has at least a photosensitive layer on a conductive support and contains a filler in the outermost surface layer.

EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated, this invention is not restrict | limited by an Example. All parts are parts by weight.
Example 1
An undercoat layer coating solution, a charge generation layer coating solution, and a charge transport layer coating solution having the following composition are sequentially applied onto an aluminum cylinder by dip coating and dried to obtain a 3.5 μm undercoat layer, 0. A 2 μm charge generation layer and a 23 μm charge transport layer were formed (photoreceptor 1).
◎ Undercoat layer coating liquid Titanium dioxide powder: 400 parts Melamine resin: 65 parts Alkyd resin: 120 parts 2-butanone: 400 parts ◎ Charge generation layer coating liquid Fluorenone bisazo pigment having the following structure: 12 parts

ポリビニルブチラール：５部
２−ブタノン：２００部
シクロヘキサノン：４００部
◎電荷輸送層塗工液
ポリカーボネート樹脂（Ｚポリカ、帝人化成製）：１０部
例示化合物Ｎｏ．１−１の第三級アミン基を有するトリフェニレン誘導体化合物：１０部
テトラヒドロフラン：１００部

Polyvinyl butyral: 5 parts 2-butanone: 200 parts Cyclohexanone: 400 parts ◎ Charge transport layer coating solution Polycarbonate resin (Z Polyca, manufactured by Teijin Chemicals): 10 parts 1-1 Triphenylene derivative compound having a tertiary amine group: 10 parts Tetrahydrofuran: 100 parts

  The electrophotographic photosensitive member produced as described above is mounted on an electrophotographic process cartridge, the charging method is a corona charging method (scorotron type), and the image exposure light source is a 655 nm semiconductor laser (LD) manufactured by Ricoh imgio MF2200. After setting the dark part potential to 800 (-V) with a remodeling machine, a repeated test equivalent to printing a total of 100,000 sheets was continuously performed. At that time, the initial image and the image after the repeated test were evaluated. Further, the bright part potential after the initial and repeated tests was also measured. The results are shown in Table 6.

Examples 2-6
In Example 1, Exemplified Compound No. Electrophotographic photosensitive members 2 to 6 were prepared and evaluated in the same manner as in Example 1 except that the compounds shown in Table 4 were used as the triphenylene derivatives having 1-1 tertiary amine. The results are also shown in Table 4.

Example 7
An electrophotographic photosensitive member 7 was produced in the same manner as in Example 1 except that the charge transport layer coating solution in Example 1 was changed to one having the following composition.
Charge transport layer coating solution Polycarbonate resin (Z Polyca, manufactured by Teijin Chemicals): 10 parts Triphenylene derivative compound having tertiary amine group of exemplified compound No. 1-1: 1 part Charge transport material of the following structural formula: 9 Part

テトラヒドロフラン：１００部

Tetrahydrofuran: 100 parts

Examples 8-12
In Example 7, electrophotographic photosensitive members 8 to 12 were all used in the same manner as in Example 7 except that the compound shown in Table 5 was used as the triphenylene derivative having the tertiary amine of Exemplified Compound No. 1-1. Were made and evaluated. The results are also shown in Table 5.

Example 13
An electrophotographic photoreceptor 13 was prepared and evaluated in the same manner as in Example 7 except that the amounts of the triphenylene derivative having a tertiary amine contained and the charge transport material were changed to the following amounts. The results are also shown in Table 6.
Triphenylene derivative compound having a tertiary amine group: 1 part Charge transport material: 7 parts

Example 14
In Example 7, the electrophotographic photoreceptor 14 was prepared and evaluated in the same manner as in Example 7 except that the amounts of the triphenylene derivative having a tertiary amine and the charge transport material were changed to the following amounts. did. The results are also shown in Table 6.
Triphenylene derivative compound having a tertiary amine group: 5 parts Charge transport material: 5 parts

Example 15
In Example 7, the electrophotographic photoreceptor 15 was produced and evaluated in the same manner as in Example 7 except that the charge transport material was changed to the following materials. The results are also shown in Table 6.

Example 16
In Example 7, the electrophotographic photosensitive member 16 was produced and evaluated in the same manner as in Example 7 except that the charge transport material was changed to the following materials. The results are also shown in Table 6.

Example 17
In Example 7, the electrophotographic photoreceptor 17 was prepared and evaluated in the same manner as in Example 7 except that the charge transporting material and binder resin contained in the charge transporting layer were changed to the following materials. The results are also shown in Table 6.
Polymer charge transport material of the following structural formula: 19 parts

Example 18
In Example 7, the electrophotographic photosensitive member 18 was prepared and evaluated in the same manner as in Example 7 except that the charge transport material and binder resin contained in the charge transport layer were changed to the following materials. The results are also shown in Table 6.
Polymer charge transport material of the following structural formula: 19 parts

Example 19
In Example 7, the electrophotographic photoreceptor 19 was prepared and evaluated in the same manner as in Example 7 except that the charge transporting substance and binder resin contained in the charge transporting layer were changed to the following materials. The results are also shown in Table 6.

Example 20
In Example 7, the electrophotographic photoreceptor 20 was prepared and evaluated in the same manner as in Example 7 except that the binder resin was changed to the following material. The results are also shown in Table 6.
Polyarylate resin (U polymer, manufactured by Unitika): 10 parts

Example 21
The electrophotographic photosensitive member 21 was prepared and evaluated in the same manner as in Example 1 except that the charge generation layer coating solution and the charge transport layer coating solution were changed to the following. The results are also shown in Table 6.
◎ Charge generation layer coating solution Oxotitanium phthalocyanine having powder XD spectrum shown in FIG. 9: 8 parts Polyvinyl butyral: 5 parts 2-butanone: 400 parts ◎ Charge transport layer coating solution Polycarbonate resin (C polycarbonate): 10 parts Compound No. 1-1 Triphenylene derivative having tertiary amine group: 1 part Charge transport material having the following structural formula: 7 parts

トルエン：７０部

Toluene: 70 parts

Example 22
An electrophotographic photosensitive member 22 was produced and evaluated in the same manner except that the charge transport material in Example 21 was changed to the following. The results are also shown in Table 6.

Comparative Example 1
A comparative electrophotographic photosensitive member was prepared in the same manner as in Example 7, except that the triphenylene derivative having a tertiary amine was changed to the following stilbene compound (amine compound described in JP-A-60-196768). 1 was made and evaluated. The results are shown in Table 7.

Comparative Example 2
In Example 7, a comparative electron was prepared in the same manner as in Example 7 except that the triphenylene derivative having a tertiary amine was not added to the coating solution for forming a charge transport layer and the weight of the charge transport material was 10 parts. Photoreceptor 2 was prepared and evaluated. The results are shown in Table 7.

Comparative Example 3
In Example 14, all the same procedures as in Example 14 except that the triphenylene derivative having a tertiary amine was changed to the following tetraphenylmethane compound (amine compound described in JP-A No. 2000-231204). Body 3 was made and evaluated. The results are shown in Table 7.

Comparative Example 4
In Example 7, a comparative electrophotographic photosensitive member 4 was prepared and evaluated in the same manner as in Example 7 except that the triphenylene derivative having a tertiary amine was used as the following hindered amine antioxidant. The results are shown in Table 7.

Comparative Example 5
A comparative electrophotographic photosensitive member was obtained in the same manner as in Example 7 except that the triphenylene derivative having a tertiary amine in Example 7 was changed to the following triphenylene compound (the triphenylene derivative described in JP-A-9-95467). 5 was prepared and evaluated. The results are shown in Table 7.

  From the above evaluation results, it was confirmed that the bright portion potential increase was small even after printing 100,000 sheets, and that the photoconductor containing the triphenylene derivative having the tertiary amine of the present invention can stably obtain a high quality image. . On the other hand, the comparative photoconductors 1, 3, and 4 have a very high bright portion potential from the beginning, causing a decrease in image density and a decrease in resolution, and the gradation is significantly decreased after printing 100,000 sheets. Image discrimination was impossible. Compared with the photoconductor of the present invention, the comparative photoconductors 2 and 5 have a relatively small increase in the bright portion potential. However, the resolution is greatly reduced due to repeated use. In particular, in the comparative photoconductor 5, it is impossible to discriminate an image because the gradation is significantly lowered.

Examples 23 to 25, Comparative Example 6
Further, the electrophotographic photoreceptors 1, 7, 13 and the comparative photoreceptor 2 were left in a desiccator adjusted to a nitrogen oxide (NOx) gas concentration of 50 ppm for 4 days, and image evaluation was performed before and after.

  From the evaluation results in Table 8, it can be seen that the resistance to oxidizing gas, that is, the suppression of reduction in resolution, is greatly improved by incorporating the triphenylene derivative having the tertiary amine of the present invention in the photoreceptor. On the other hand, the comparative photoreceptor 2 has good initial image quality, but it can be seen that the resolution is significantly lowered by the oxidizing gas.

1 is an example of a cross-sectional view of an electrophotographic photosensitive member of the present invention. It is another example of sectional drawing of the electrophotographic photosensitive member of this invention. It is another example of sectional drawing of the electrophotographic photosensitive member of this invention. It is another example of sectional drawing of the electrophotographic photosensitive member of this invention. It is another example of sectional drawing of the electrophotographic photosensitive member of this invention. It is the schematic which shows an example of the electrophotographic process and electrophotographic apparatus of this invention. It is the schematic which shows the other example of the electrophotographic process and electrophotographic apparatus of this invention. FIG. 2 is a schematic diagram illustrating an example of a process cartridge for an image forming apparatus according to the present invention. It is a figure which shows the XD spectrum of the oxotitanium phthalocyanine used in the Example.

Explanation of symbols

DESCRIPTION OF SYMBOLS 1 Photoconductor 2 Static elimination lamp 3 Charger 4 Eraser 5 Image exposure part 6 Developing unit 7 Pre-transfer charger 8 Registration roller 9 Transfer paper 10 Transfer charger 11 Separation charger 12 Separation claw 13 Pre-cleaning charger 14 Fur brush 15 Cleaning blade 16 Photoconductor 17 Charging Charger 18 Cleaning Brush 19 Image Exposure Unit 20 Developing Roller 21 Photoconductor 22a Driving Roller 22b Driving Roller 23 Charging Charger 24 Image Exposure Source 25 Transfer Charger 26 Pre-Cleaning Exposure 27 Cleaning Brush 28 Static Discharge Light Source 31 Conductive Support 33 Photosensitive Layer 35 charge generation layer 37 charge transport layer 39 protective layer

Claims (14)

An electrophotographic photoreceptor, wherein a photosensitive layer containing a triphenylene derivative having a tertiary amine represented by the following general formula (1) as a component is provided on a conductive support.

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ are substituted or unsubstituted alkyl groups, or substituents represented by the following general formula Y1

(In the general formula Y1, R ⁷ represents a substituted or unsubstituted alkylene group, and R ⁸ and R ⁹ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon ring group. May be the same as or different from each other, provided that one of R ⁸ and R ⁹ is a substituted or unsubstituted alkyl group, and R ⁸ and R ⁹ are bonded to each other and contain a nitrogen atom. An unsubstituted heterocyclic group may be formed), which may be the same or different. However, at least one of R ^{1 to} R ⁶ is Y1. X represents an oxygen atom or a sulfur atom. ] An electrophotographic photoreceptor, wherein a photosensitive layer containing a triphenylene derivative having a tertiary amine represented by the following general formula (2) as an active ingredient is provided on a conductive support.

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ are a substituted or unsubstituted alkyl group, or a substituent represented by the following general formula Y1,

(In the general formula Y1, R ⁷ is a substituted or unsubstituted alkylene group. Also, R ⁸ and R ⁹ are substituted or unsubstituted alkyl groups, substituted or unsubstituted aromatic hydrocarbon ring groups. Each of which may be the same or different, provided that one of R ⁸ and R ⁹ is a substituted or unsubstituted alkyl group, and R ⁸ and R ⁹ are bonded to each other and contain a nitrogen atom. A substituted or unsubstituted heterocyclic group may be formed), which may be the same or different. However, at least one of R ^{1 to} R ⁶ is Y. ] An electrophotographic photoreceptor, wherein a photosensitive layer containing a triphenylene derivative having a tertiary amine represented by the following general formula (3) as an active ingredient is provided on a conductive support.

[Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ are substituted or unsubstituted alkyl groups, or substituents represented by the following general formula Y2.

(In the general formula Y2, R ⁷ and R ⁸ represent a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon ring group, and may be the same or different. However, R ⁷ , Any one of R ⁸ is a substituted or unsubstituted alkyl group, and R ⁷ and R ⁸ may be bonded to each other to form a substituted or unsubstituted heterocyclic group containing a nitrogen atom.) Which may be the same or different. However, at least one of R ^{1 to} R ⁶ is Y. ] The photosensitive layer contains at least one of a charge transport material and a triphenylene derivative having a tertiary amine represented by the general formulas (1) to (3). The electrophotographic photosensitive member according to any one of items 1 to 3. The electrophotographic photoreceptor according to claim 4, wherein the charge transport material is a stilbene compound represented by the following general formula (20).

[Wherein n represents an integer of 0 or 1, R ¹ represents a hydrogen atom, an alkyl group, or a substituted or unsubstituted phenyl group, Ar ¹ represents a substituted or unsubstituted aromatic hydrocarbon ring group, R ⁵ Represents an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring group, and Ar ¹ and R ⁵ may jointly form a ring. A is an expression

Or

A substituent represented by
{Wherein R ² is a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom or a formula

Wherein R ³ and R ⁴ represent a substituted or unsubstituted aromatic hydrocarbon ring group, and R ³ and R ⁴ may be the same or different and may form a ring, and m represents Represents an integer of 1 to 3, and R ² may be the same or different when it is 2 or more. }
It represents a 9-anthryl group or a substituted or unsubstituted carbazolyl group. When n is 0, A and R ¹ may form a ring together. ] The electrophotographic photoreceptor according to claim 4, wherein the charge transport material is an aminobiphenyl compound represented by the following general formula (25).

(Wherein R ¹ , R ³ and R ⁴ are a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted group. R ² represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group or a halogen atom, and k, l, m and n are integers of 1, 2, 3 or 4, When R is an integer of 2, 3 or 4, the R ¹ , R ² , R ³ and R ⁴ may be the same or different.) The electrophotographic photosensitive member according to claim 4, wherein the charge transport material is a polymer charge transport material. 8. The electrophotographic photosensitive member according to claim 7, wherein the polymer type charge transport material is a material represented by the following general formula (II).

[Wherein R ₇ and R ₈ represent substituted or unsubstituted aromatic ring groups, and Ar ₁ , Ar ₂ and Ar ₃ represent the same or different aromatic ring groups. k, j represents the composition, 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, and n represents the number of repeating units and is an integer of 5 to 5000.
X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula S1 or S2.

(In the general formula S1, R ₁₀₁ and R ₁₀₂ each independently represents a substituted or unsubstituted alkyl group, an aromatic ring group or a halogen atom. L, m are integers of 0 to 4, Y is a single bond, A linear, branched or cyclic alkylene group having 1 to 12 carbon atoms, —O—, —S—, —SO—, —SO ₂ —, —CO—, —CO—O—Z—O—CO -(Wherein Z represents an aliphatic divalent group), in general formula S2, a is an integer of 1 to 20, b is an integer of 1 to 2000, and R ₁₀₃ and R ₁₀₄ are substituted or unsubstituted. R ₁₀₁ and R ₁₀₂ , R ₁₀₃ and R ₁₀₄ may be the same or different from each other. ). ] The electrophotographic photosensitive member according to claim 7, wherein the polymer type charge transport material is a material represented by the following general formula (XI).

(In the formula, Ar ₁ , Ar ₂ , Ar ₃ , Ar ₄ and Ar ₅ represent a substituted or unsubstituted aromatic ring group, Z represents an aromatic ring group or —Ar ₆ —Za—Ar ₆ —, and Ar ₆ represents a substituted group. Or an unsubstituted aromatic ring group, Za represents O, S or an alkylene group, R and R ′ represent a linear or branched alkylene group, m represents 0 or 1, k, j, n and X represent Same as formula.) The electrophotographic photosensitive member according to claim 1, wherein at least charging, image exposure, development, and transfer are repeatedly performed on the electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is the electrophotographic photosensitive member according to claim 1. And an electrophotographic method. A so-called digital electronic device in which at least charging, image exposure, development, and transfer are repeated on an electrophotographic photosensitive member, and an electrostatic latent image is written on the photosensitive member by an LD or LED during image exposure. 10. An electrophotographic method according to claim 1, wherein the electrophotographic photoreceptor is the electrophotographic photoreceptor according to any one of claims 1 to 9. An electrophotographic apparatus comprising at least a charging unit, an image exposing unit, a developing unit, a transfer unit, and an electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is any one of claims 1 to 9. An electrophotographic apparatus characterized by being a body. In an electrophotographic apparatus comprising at least a charging unit, an image exposing unit, a developing unit, a transferring unit, and an electrophotographic photosensitive member, an electrostatic latent image is formed on the photosensitive member by using an LD or an LED as the image exposing unit. 10. A so-called digital electrophotographic apparatus in which writing is performed, wherein the electrophotographic photoreceptor is the electrophotographic photoreceptor according to any one of claims 1 to 9. An electrophotographic photosensitive member comprising at least an electrophotographic photosensitive member, wherein the electrophotographic photosensitive member is the electrophotographic photosensitive member according to any one of claims 1 to 9. Process cartridge for equipment.

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